16250-37-6

Basic information

• Product Name: N-Allylformamide
• Synonyms: N-Allylformamide;Nsc77938;N-(Prop-2-en-1-yl)formamide;N-2-propen-1-ylFormamide;N-prop-2-enylformamide;allylformamide
• CAS NO: 16250-37-6
• Molecular Formula: C₄H₇NO
• Molecular Weight: 85.1
• Product Categories: Aliphatics;Aldehydes
• Mol File: 16250-37-6.mol

Chemical Properties

• Boiling Point: 223.1 °C at 760 mmHg
• Flash Point: 114.4 °C
• Appearance: /
• Density: 0.888 g/cm³
• Vapor Pressure: 0.0979mmHg at 25°C
• Refractive Index: 1.416
• CAS DataBase Reference: N-Allylformamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-Allylformamide(16250-37-6)
• EPA Substance Registry System: N-Allylformamide(16250-37-6)

Safety Data

• Hazardous Substances Data: 16250-37-6(Hazardous Substances Data)

Usage

Uses

Used in Polymer Production:
N-Allylformamide is used as a monomer for the production of polymers, contributing to the formation of polymer chains that are essential in various industrial applications.
Used in Pharmaceutical Industry:
N-Allylformamide is used as a precursor in the synthesis of pharmaceuticals, playing a vital role in the development of new drugs and medicinal compounds.
Used in Agricultural Products:
In the agricultural sector, N-Allylformamide is utilized as a precursor for the production of agrochemicals, which are essential for crop protection and enhancement of agricultural yields.
Used in Fine Chemicals Synthesis:
N-Allylformamide is employed as an important intermediate in the synthesis of various fine chemicals, which are used in a wide range of applications, including fragrances, dyes, and other specialty chemicals.

InChI:InChI=1/C4H7NO/c1-2-3-5-4-6/h2,4H,1,3H2,(H,5,6)

Upstream product

• 64-18-6 formic acid 
• 57-06-7 N-allyl isothiocyanate 
• 1493-02-3 formyl fluoride 
• 107-11-9 1-amino-2-propene 
• 109-94-4 formic acid ethyl ester 
• 124-38-9 carbon dioxide 
• 123-91-1 1,4-dioxane 
• 1476-23-9 allylisocyanate 
• 1118-02-1 trimethylsilyl isocyanate 
• 70122-89-3 tert-butyl allyl carbonate 
• 802294-64-0 propionic acid 
• 107-31-3 Methyl formate 
• 68-12-2 N,N-dimethyl-formamide 

Downstream Products

• 627-37-2 N-methyl-N-allylamine 
• 65608-73-3 1-allyl-3-benzylurea 
• 130012-62-3 N-prop-2-enylbenzocarbothioamide 
• 1588513-09-0 C₃₂H₃₅N₆O₅⁽¹⁺⁾*BF₄^(1-) 
• 1588513-04-5 C₃₀H₃₂N₇O₆⁽¹⁺⁾*BF₄^(1-) 
• 43219-52-9 (E)-N-(3-Phenyl-2-propenyl)formamid 
• 107960-67-8 (E)-N-(3-(4-methoxyphenyl)allyl)formamide 
• 1198802-38-8 C₁₂H₂₀N₂O₃ 
• 30698-14-7 N-(N'-Phenylformimidoyl)N-allylformamid 

Relevant articles and documents

Site-Selective Installation of N?-Modified Sidechains into Peptide and Protein Scaffolds via Visible-Light-Mediated Desulfurative C–C Bond Formation

Post-translational modifications (PTMs) enhance the repertoire of protein function and mediate or influence the activity of many cellular processes. The preparation of site-specifically and homogeneously modified proteins, to apply as tools to understand the biological role of PTMs, is a challenging task. Herein, we describe a visible-light-mediated desulfurative C(sp3)–C(sp3) bond forming reaction that enables the site-selective installation of N?-modified sidechains into peptides and proteins of interest. Rapid, operationally simple, and tolerant to ambient atmosphere, we demonstrate the installation of a range of lysine (Lys) PTMs into model peptide systems and showcase the potential of this technology by site-selectively installing an N?Ac sidechain into recombinantly expressed ubiquitin (Ub).

Catalyst freeN-formylation of aromatic and aliphatic amines exploiting reductive formylation of CO2using NaBH4

Herein, we report a sustainable approach forN-formylation of aromatic as well as aliphatic amines using sodium borohydride and carbon dioxide gas. The developed approach is catalyst free, and does not need pressure or a specialized reaction assembly. The reductive formylation of CO2with sodium borohydride generates formoxy borohydride speciesin situ, as confirmed by1H and11B NMR spectroscopy. Thein situformation of formoxy borohydride species is prominent in formamide based solvents and is critical for the success of theN-formylation reactions. The formoxy borohydride is also found to promote transamidation reactions as a competitive pathway along with reductive functionalization of CO2with amine leading toN-formylation of amines.

KOtBu-Promoted Transition-Metal-Free Transamidation of Primary and Tertiary Amides with Amines

This work discloses transamidation of primary and tertiary amides with a range of aryl, heteroaryl, and aliphatic amines using potassium tert-butoxide. The reaction proceeds at room temperature under transition-metal-free conditions providing secondary amides in high yields. Moreover, reaction of cyclopropyl amine with tertiary amides proceeds with ring-opening to provide a rapid access to enamides.

A Peptide Backbone Stapling Strategy Enabled by the Multicomponent Incorporation of Amide N-Substituents

The multicomponent backbone N-modification of peptides on solid-phase is presented as a powerful and general method to enable peptide stapling at the backbone instead of the side chains. This work shows that a variety of functionalized N-substituents suitable for backbone stapling can be readily introduced by means of on-resin Ugi multicomponent reactions conducted during solid-phase peptide synthesis. Diverse macrocyclization chemistries were implemented with such backbone N-substituents, including the ring-closing metathesis, lactamization, and thiol alkylation. The backbone N-modification method was also applied to the synthesis of α-helical peptides by linking N-substituents to the peptide N-terminus, thus featuring hydrogen-bond surrogate structures. Overall, the strategy proves useful for peptide backbone macrocyclization approaches that show promise in peptide drug discovery.

Mild Access to N-Formylation of Primary Amines using Ethers as C1 Synthons under Metal-Free Conditions

A new synthetic protocol has been developed for the synthesis of N-formamide derivatives using ethers as a C1 synthon under metal-free reaction conditions. The reaction is proposed to proceed through C?H functionalization, C?O cleavage, and C?N bond formation. This protocol is applicable to a variety of primary amines resulting in N-formamides in moderate to good yields. 1,4-dioxane was chosen as best C1 synthon after screening with various ethers. Mechanistic studies disclosed that the reaction proceeds through a radical pathway. While using α-amino ketones a α-alkylation product was formed rather than formylation. By replacing dioxane with Tetramethylethylenediamine (TMEDA) under standard conditions also gave the N-formamide derivatives in moderate yields. (Figure presented.).

Chemoselective Schwartz Reagent Mediated Reduction of Isocyanates to Formamides

Addition of the in situ generated Schwartz reagent to widely available isocyanates constitutes a chemoselective, high-yielding, and versatile approach to the synthesis of variously functionalized formamides. Steric and electronic factors or the presence of sensitive functionalities (esters, nitro groups, nitriles, alkenes) do not compromise the potential of the method. Full preservation of the stereochemical information contained in the starting materials is observed. The use of formamides in the nucleophilic addition of organometallic reagents (Chida-Sato allylation, Charette-Huang addition to imidoyl triflate activated amides, Matteson homologation of boronic esters) is briefly investigated.

Palladium-Catalyzed Synthesis of Allylic Ureas via an Isocyanate Intermediate

A palladium-catalyzed coupling of allylic carbonates with trimethylsilylisocyanate to provide allylic isocyanates is reported. Amines are added in a second step to yield allylic ureas in this one-pot procedure. Use of a bidentate phosphine ligand with a large bite angle was found to be important in this transformation. The scope of allylic carbonates has been examined, as well as amines compatible with these reaction conditions.

Formamide Synthesis through Borinic Acid Catalysed Transamidation under Mild Conditions

A highly efficient and mild transamidation of amides with amines co-catalysed by borinic acid and acetic acid has been reported. A wide range of functionalised formamides was synthesized in excellent yields, including important chiral α-amino acid derivatives, with minor racemisation being observed. Experiments suggested that the reaction rely on a cooperative catalysis involving an enhanced boron-derived Lewis acidity rather than an improved Br?nsted acidity of acetic acid. Amide bonds are reputedly difficult to activate due to their high resonance stabilization. An unusual mild activation of dimethylformamide and formamide by borinic acid 1 (see scheme), illustrated by a general formylation of a wide range of amines, including chiral α-amino esters, has been reported.

A Modular Formal Total Synthesis of (±)-Cycloclavine

Cycloclavine is a clavine-type Ergot alkaloid noteworthy for its unique pentacyclic skeleton featuring a 3-azabicyclo[3.1.0]hexane substructure. A short convergent route to the racemic alkaloid is described which comprises only eight linear steps and requires only four chromatographic purifications. The two key building blocks can be prepared in high yield from commercially available starting materials. Two consecutive coupling reactions, namely a selective alkylation of a dienolate and a Heck reaction, are the key steps of the reaction sequence. (Chemical Equation Presented).

Synthesis and characterization of novel carbene complexes of phosphorus(V) fluorides with potential liquid-crystalline properties

A series of novel push-push I and push-pull II carbene-stabilized complexes of phosphorus(V) fluorides bearing substituents with liquid-crystalline properties were synthesized by the oxidative addition of difluoroamines to phosphorus(III) halides. These octahedral complexes were characterized by NMR spectroscopy and X-ray analysis.